


Feels Like The First Time

by gothpandaotaku



Category: Supernatural
Genre: Alpha Dean, Alpha/Beta/Omega Dynamics, Anal Sex, Angst and Porn, Awkward First Times, Bottom Sam, First Time, Fluff and Angst, Loss of Virginity, M/M, Mild Blood, Omega Jared/Sam Challenge 2016, Omega Sam, Omega Sam Winchester, Rough Sex, Underage Sex, Weecest
Language: English
Status: Completed
Published: 2016-12-11
Updated: 2016-12-11
Packaged: 2018-09-07 19:02:46
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,096
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8812471
Author URL: https://archiveofourown.org/users/gothpandaotaku/pseuds/gothpandaotaku
Summary: Dean really should get a medal for waiting this long.





	

**Author's Note:**

> For Day 4 of the challenge, First Time

Dean really should get a medal for waiting this long.

Sixteen long, long years he’d waited for this. To have his Omega baby brother spread out before him, like a buffet, just waiting to be devoured. Sam had been begging for years, ever since his first heat at the age of twelve, to be knotted by his big brother. Somehow, Dean had managed to resist, although not entirely. He’d lost count of how many times he’s finger-fucked Sam and sucked him off during his heats.

But now, on Sam’s sixteenth birthday, he couldn’t hold back any longer. Tonight he was going to claim what was his, mark Sam as _his_.

“Deeeeeean, quit teasing,” Sam whined, spreading his legs obscenely wide so that Dean got a perfect view of the beautiful, dusty pink hole waiting for him. Waiting to be filled.

“I got you,” Dean smirked at Sam’s eagerness, grabbing the small bottle of lube on the nightstand and squirting a generous amount onto his palm. He climbed on the bed and got on his knees, his face now just inches away from heaven.

Sam trembled as Dean blew a warm breath over his entrance. A trail of slick slid down from his hole to his thighs.

“Already so wet for me, Baby Boy,” Dean whispered, voice low and rough, in Sam’s ear. He nipped at Sam’s neck and Sam felt himself release more slick.

“Oh god,” Sam moaned when Dean’s finger traced around his entrance. “Please please please…”

“You can call me Dean.”

“Shut up,” Sam laughed, which quickly broke off into another moan when a long finger abruptly pushed inside him. “Fuck yeah. More, more.”

Dean took his time working two more fingers into Sam, wanting to the enjoy the anticipation. He fucked Sam with his fingers, massaging his prostate just enough to have him writhing beneath him and begging to come, but not enough for release.

When Sam’s voice was hoarse from begging Dean to fuck him and Dean’s dick was hard enough to cut diamonds, he removed his fingers and positioned his cock at Sam’s entrance. “Ready, Sammy? You want your big brother to fuck you?”

“Yes, please, please fuck me big brother, please,” Sam panted, sure he was about to go crazy with pleasure and needing release.

“Big brother’s job to take care of little brother,” Dean grinned as he slowly pushed the head of his thick cock inside Sam.

Sam bit his lip at the discomfort. Even with all the slick, it still hurt a little. Dean was _big_ ; three fingers didn’t even compare. “Ah!” he cried out in pain when Dean pushed in a little too fast.

Dean froze. “S-Sorry, sorry. Do you want me to stop?” He was only halfway inside Sam and already the tight, wet heat felt _amazing_ , but he’d do anything for Sam.

“No, just… go slow, please.”

Inch by agonizingly slow inch, Dean gave Sam his cock until he was finally balls deep inside him. “Oh fuck,” Dean moaned. He resisted the inner Alpha inside him that just wanted to fuck Sam into the mattress, and waited a few moments for Sam to adjust.

Sam felt full, so full it was nearly overwhelming, but at the same time it felt _really fucking good_. He nodded at Dean to let him know he could move.

Dean pulled out until just the head of his cock was inside Sam and then shoved back in. He felt Sam gasp at his first thrust, and did it again. “Fuck Sammy, you feel _so good_. Fucking perfect. Like you were made for me.” Sam was tight and hot and _wet_ and _perfect_ around him, already taking his dick like a champ, lowering himself down on his cock when Dean thrust up. He let out a long, drawn-out moan worthy of a pornstar as Dean’s next thrust nailed his prostate—

And that was it. Dean felt his orgasm hit like a freight train.  He rocked his hips as he emptied his seed deep inside his little brother, his knot swelling and locking him in place for the time being. “Sammy, Sammy, Sammy!” He groaned into the crook of Sam’s neck.

“Um, Dean? Did you just…?”

The haze of orgasm lifted and Dean realized what he’d done. He’d just come. After three minutes. Like a fucking virgin. Sam, _an actual virgin_ , hadn’t even come that fast!

“Uh, I’m just gonna, sorry.” About to die from embarrassment and blushing like he’d never blushed in his life, Dean moved to pull out, momentarily forgetting that his knot wouldn’t let him.

Sam grabbed Dean’s wrist before he could. “Dean, hey, stop.” He pulled Dean in closer and tenderly cupped his cheek before kissing him. “It’s alright. Nothing to be embarrassed about, I was about to come myself. And besides, it’s kind of flattering, actually.”

“Yeah? It’s just, been waiting for this so long you know,” Dean said quietly, ears and face an adorable shade pink, and Sam just had to kiss him again.

“Me too. Now, what do you say? Think you can get it up again to fuck your little brother right, old man?” Sam teased, knowing that Dean was still hard.

“Oh, you’re gonna pay for that, you little Bitch,” Dean growled.

“Promises, promises, Jerk.”

Sam clamped his muscles around Dean’s hard cock still nestled inside him. Dean gave a wicked grin before beginning to fuck him in earnest.

Done with foreplay, Dean set a fast and passionate pace, fucking into Sam so hard he was pushed up the bed and the headboard banged against the wall. He pinched and licked at Sam’s pointed nipples, knowing they were a sensitive spot. Sam screamed when Dean sharpened the angle so his cock hit his sweet spot on every thrust.

“Yes, yes, yes,” Sam moaned. “ _Harder._ ”

“You like it,” _thrust_ “when big brother,” _thrust_ “fucks you,” _thrust_ “on his knot” _thrust_ “huh, Sammy?” Dean grinned and obliged, fucking Sam even harder. He wrapped a hand around Sam’s dick and began jerking him off in time with his thrusts.

“Dean, I’m gonna,” Sam gasped, nearly incoherent with pleasure at this point.

“Come for me, Baby Boy.”

Sam came, screaming Dean’s name at the top of his lungs, white pearls of come landing on his chest. Dean licked them and continued to fuck Sam through his orgasm, until the tightening of Sam’s muscles around his cock became too much and his own orgasm hit. He filled his baby brother with his come, again, and the thought was enough to wring another small orgasm out of him.

Exhausted, Dean practically collapsed on top of Sam. Sam snuggled into him and appeared to already be drifting off to sleep. But the sweat and stickiness between their bodies made Dean uncomfortable enough that as soon as his knot deflated enough to pull out of Sam he got to his feet in order to clean them up, heading into the adjoining bathroom.

Sam whined at the loss of warmth. He shifted around on the bed in search of his brother. Dean came back into the room and snorted. “I’m here Sammy, let’s get you cleaned up.” He pulled back the sheets and froze, dropping the washcloth in his hand.

A small puddle of blood dripped down Sam’s thighs and stained the white motel sheets.

Dean’s stomach lurched. He dashed back into the bathroom and barely made it the toilet before he retched.

“Dean? What’s going on? What’s wrong?” Sam asked, blinking his eyes open, sensing something was wrong with his Alpha. He heard his brother retch and made his way to the bathroom on shaky legs. He dropped to his knees next to Dean, his head resting on the cool ceramic of the toilet seat. “Dean, you okay?” He gently laid a comforting hand on Dean’s shoulder.

Dean jerked away as if he’d been burned.

“What’s wrong? Answer me!” Sam snapped.

“Look at yourself,” Dean growled. “ _I hurt you._ ”

Sam looked down at himself. His eyes widened, surprised to find a little trickle of bright red blood running down his thighs. “Huh.”

“That’s all you have to say? I hurt you. _I fucking hurt you!_ ” Dean started off shouting in anger, but the fight left him almost immediately and his face grew pale. “Oh god, Baby Boy, I’m so so so sorry. I’m sorry. I didn’t mean to hurt you. I understand if you don’t want to be with me again, but—but please, don’t leave me. _I’m sorry._ ”

His brother was on his knees before him, _begging_ him to forgive him, and Sam… didn’t know what to do. Dean was on the verge of a full out panic attack. A sick feeling twisted in his gut. This was about something deeper than being a little rough in bed.

Sam took a deep breath and blinked back the tears threatening to fall. He needed to be strong for Dean. “Hey De, it’s okay. It’s okay. Calm down,” he said in a soft, soothing voice. The voice and scent of an Omega was often soothing to Alphas, so he got as close as Dean would let him. “Take a nice, deep breath, can you do that for me?” He repeatedly demonstrated taking a deep breath and after a few times Dean followed suit. “Good, that’s good.”

Once he got Dean mostly calmed down, Sam said in the same soothing voice, “I am perfectly fine, alright? Yes, it burns a little now that the endorphins have run out, but I am _fine._ I want you to repeat it after me.”

“But-”

“Repeat it.”

Dean looked down at the floor as he said it. “You’re… you’re fine.”

Sam nodded. “Good.” Tenderly, lovingly, he ran a hand down Dean’s face and held it there. Slowly, Dean brought a hand up to hold over Sam’s as tears streamed down his perfect face.

“I’m sorry,” Dean whispered. “I promise it won’t happen again, I promise.”

“Shhhh.” Sam put a finger over Dean’s mouth. “There’s nothing to be sorry about. No need to apologize. It’s been established that I’m fine right?” Dean hesitantly nodded. “Dean, listen to me. It’s relatively common for Omega’s to bleed their first time.” He shushed Dean when it looked like he was going to argue again. “It’s true. You know I do my research. And remember, I _asked_ for you to be rough, and it felt very good. And it doesn’t even hurt that bad, okay? Maybe next time we could stand to do a little more prep, would that make you feel better?”

“N—Next time?” Dean asked quietly as if he was afraid of the answer.

“Yes, De, next time. I’m not leaving you. _Ever_.”

Dean practically melted into Sam’s waiting arms, sobbing into his neck. “You won’t leave me? You’re not gonna leave me?”

“Never ever.”

“Never ever?”

“ _Never ever_.”

It took a long time to get Dean calmed down enough that his sobs turned to sniffles, but Sam held him as long as it took. He suggested they go to sleep and Dean nodded his agreement, still looking a little dazed, but better.

Sam tried to stand, but his legs were still pretty shaky, and now stiff from being on the cold tile floor. Knowing how much Dean secretly loved to take care of him, and knowing that was exactly what he needed right now, he saw an opportunity. “Dean?”

Dean, already halfway to the door, turned around.

“Carry me!” Sam batted his doe eyes and made grabby hands at his brother, like he used to as a small child.

He actually managed to get Dean to crack a little smile.

Dean picked him up gently, cradling him to his chest like he was the most precious thing in the world, and Sam had never felt safer or more loved.

They crawled under the covers of the bed (Sam threw the sheets in the trash) and tangled their limbs together. Dean buried his face in the crook of Sam’s neck, wrapping his arms around Sam’s waist. Usually Dean was the one accusing him of being an octopus, but he sensed his brother needed the comfort tonight. A small part of him, the Omega part, even reveled in it.

“Hey De?”

“Mmmm.”

“I really really enjoyed what we did tonight. It was perfect. I love you.”

It could have been his imagination, Dean was already half asleep, but he swore he felt Dean mouth _I love you_ against his neck.

It was messy, and awkward, and rough, and a little confusing… but their first time was nothing short of perfect.

 

 

**Author's Note:**

> As always, I'd love to hear your thoughts <3


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